US6436371B2 - Oral composition - Google Patents

Oral composition Download PDF

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Publication number
US6436371B2
US6436371B2 US09/805,524 US80552401A US6436371B2 US 6436371 B2 US6436371 B2 US 6436371B2 US 80552401 A US80552401 A US 80552401A US 6436371 B2 US6436371 B2 US 6436371B2
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United States
Prior art keywords
oral composition
composition
hydroxypropiophenone
wintergreen
alkaline
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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US09/805,524
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US20010031246A1 (en
Inventor
Neil Kilcullen
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Unilever Home and Personal Care USA
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Unilever Home and Personal Care USA
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Assigned to UNILEVER HOME & PERSONAL CARE USA, DIVISION OF CONOPCO, INC. reassignment UNILEVER HOME & PERSONAL CARE USA, DIVISION OF CONOPCO, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KILCULLEN, NEIL
Publication of US20010031246A1 publication Critical patent/US20010031246A1/en
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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35Ketones, e.g. benzophenone

Definitions

  • the present invention relates to an oral composition comprising 2′-hydroxypropiophenone.
  • flavours used in oral care formulations are mint. Further, there are many different flavour ingredients which effect several different minty flavours to the consumer, for example, peppermint oil, spearmint oil and wintergreen oil to name a few. Wintergreen oil is a particularly popular flavour material and is commonly used in oral care formulations, particularly toothpastes, all over the world.
  • flavour molecules which are usually used to impart a wintergreen flavour to such oral compositions are only ever used in toothpastes which have a substantially neutral pH, for example, the paste marketed by the applicant under the brand name ‘Close-up®’.
  • the present invention provides an oral composition including a wintergreen flavour imparting ingredient and having an alkaline pH, wherein the wintergreen flavour imparting ingredient is 2′-hydroxypropiophenone.
  • 2′-hydroxypropiophenone is commercially available from Sigma-Aldrich Company Ltd., The Old Brickyard, Gillingham, Dorset SP12 4XT, United Kingdom. A synthesis for the compound may be found in Org. Synth. 13, 90 (1933).
  • the pH of the composition is alkaline. By this is meant that it is not neutral, or substantially neutral, and ranges from about 7.5 to about 12.
  • the pH is greater than 7.5 and preferably above 8.5.
  • the oral composition according to the invention typically comprises from 0.0001 to 1% by weight 2′-hydroxypropiophenone, preferably from 0.001 to 0.75% and especially from 0.1 to 0.2% by weight.
  • the invention relates to a method for imparting a wintergreen flavour to an oral composition of alkaline pH by incorporation into the composition 2′-hydroxypropiophenone.
  • the oral composition according to the invention typically comprises further ingredients which are common in the art, such as:
  • antimicrobial agents e.g. Triclosan, chlorhexidine, copper- , zinc- and stannous salts such as zinc citrate, zinc sulphate, zinc glycinate, sodium zinc citrate and stannous pyrophosphate, sanguinarine extract, metronidazole, quaternary ammonium compounds, such as cetylpyridinium chloride; bis-guanides, such as chlorhexidine digluconate, hexetidine, octenidine, alexidine; and halogenated bisphenolic compounds, such as 2,2′ methylenebis-(4-chloro-6-bromophenol);
  • anti-inflammatory agents such as ibuprofen, flurbiprofen, aspirin, indomethacin etc.;
  • anti-caries agents such as sodium- and stannous fluoride, aminefluorides, sodium monofluorophosphate, sodium trimeta phosphate and casein;
  • plaque buffers such as urea, calcium lactate, calcium glycerophosphate and strontium polyacrylates; vitamins such as Vitamins A, C and E;
  • desensitising agents e.g. potassium citrate, potassium chloride, potassium tartrate, potassium bicarbonate, potassium oxalate, potassium nitrate and strontium salts;
  • anti-calculus agents e.g. alkali-metal pyrophosphates, hypophosphite-containing polymers, organic phosphonates and phosphocitrates etc.;
  • biomolecules e.g. bacteriocins, antibodies, enzymes, etc.
  • flavours e.g. peppermint and spearmint oils
  • preservatives e.g. methyl paraben
  • opacifying agents e.g. titanium dioxide
  • colouring agents e.g. FD&C Blue No. 1, FD&C Yellow No. 5;
  • pH-adjusting agents e.g. monosodium phosphate, trisodium phosphate, sodium hydroxide, sodium carbonate;
  • sweetening agents e.g. sodium saccharin, aspartame
  • pharmaceutically acceptable carriers e.g. starch, sucrose, water or water/alcohol systems etc.;
  • surfactants such as anionic, nonionic, cationic and zwitterionic or amphoteric surfactants
  • particulate abrasive materials such as silicas, aluminas, calcium carbonates, dicalciumphosphates, calcium pyrophosphates, hydroxyapatites, trimetaphosphates, insoluble hexametaphosphates and so on, including agglomerated particulate abrasive materials, usually in amounts between 3 and 60% by weight of the oral care composition;
  • humectants such as glycerol, sorbitol, propyleneglycol, xylitol, lactitol etc.;
  • binders and thickeners such as sodium carboxymethyl-cellulose, xanthan gum, gum arabic etc. as well as synthetic polymers such as polyacrylates and carboxyvinyl polymers such as Carbopol®;
  • polymeric compounds which can enhance the delivery of active ingredients such as antimicrobial agents can also be included.
  • examples of such polymers are copolymers of polyvinylmethylether with maleic anhydride and other similar delivery enhancing polymers, e.g. those described in DE-A-3,942,643 (Colgate);
  • bleaching agents such as peroxy compounds e.g. potassium peroxydiphosphate, effervescing systems such as sodium bicarbonate/citric acid systems, colour change systems, and so on.
  • Liposomes may also be used to improve delivery or stability of active ingredients.
  • the oral compositions may be in any form common in the art, e.g. toothpaste, gel, mousse, aerosol, gum, lozenge, powder, cream, etc. and may also be formulated into systems for use in dual-compartment type dispensers.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)

Abstract

Oral composition comprises a wintergreen flavor imparting ingredient and having an alkaline pH, wherein the wintergreen flavor imparting ingredient is 2′-hydroxypropiophenone.

Description

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to an oral composition comprising 2′-hydroxypropiophenone.
2. The Related Art
One of the commonest flavours used in oral care formulations is mint. Further, there are many different flavour ingredients which effect several different minty flavours to the consumer, for example, peppermint oil, spearmint oil and wintergreen oil to name a few. Wintergreen oil is a particularly popular flavour material and is commonly used in oral care formulations, particularly toothpastes, all over the world.
The flavour molecules which are usually used to impart a wintergreen flavour to such oral compositions are only ever used in toothpastes which have a substantially neutral pH, for example, the paste marketed by the applicant under the brand name ‘Close-up®’.
It is well known in toothpaste manufacture that the main ingredient in wintergreen flavour, methyl salicylate, is unstable in alkaline pH ranges.
This presents a problem since some of the more popular oral care compositions are at a substantially alkaline pH. For example, bicarbonate toothpastes are marketed by many of the oral care consumer products suppliers and are only ever made at substantially alkaline pH ranges. Further, where calcium carbonate is used as a polishing agent, for example, in the developing and emerging markets, the general pH of a formulation is also substantially alkaline, often as high as 10.
The prior art literature also refers to wintergreen oil as a flavour ingredient. WO 98/31242 (Wrigley) discloses the use of 2′-hydroxypropiophenone as a substitute for the major wintergreen ingredient methyl salicylate. However, no mention is made of the fact that 2′-hydroxypropiophenone can also be used to overcome the disadvantages of methyl salicylate as a wintergreen flavour ingredient where the pH is alkaline.
It is an object of the invention to provide an oral composition which is stable, has a wintergreen flavour and is at an alkaline pH.
SUMMARY OF THE INVENTION
Accordingly, the present invention provides an oral composition including a wintergreen flavour imparting ingredient and having an alkaline pH, wherein the wintergreen flavour imparting ingredient is 2′-hydroxypropiophenone.
2′-hydroxypropiophenone is commercially available from Sigma-Aldrich Company Ltd., The Old Brickyard, Gillingham, Dorset SP12 4XT, United Kingdom. A synthesis for the compound may be found in Org. Synth. 13, 90 (1933).
It is an essential feature of the invention that the pH of the composition is alkaline. By this is meant that it is not neutral, or substantially neutral, and ranges from about 7.5 to about 12.
In a particular embodiment the pH is greater than 7.5 and preferably above 8.5.
The oral composition according to the invention typically comprises from 0.0001 to 1% by weight 2′-hydroxypropiophenone, preferably from 0.001 to 0.75% and especially from 0.1 to 0.2% by weight.
In a further aspect, the invention relates to a method for imparting a wintergreen flavour to an oral composition of alkaline pH by incorporation into the composition 2′-hydroxypropiophenone.
DETAILED DESCRIPTON
The oral composition according to the invention typically comprises further ingredients which are common in the art, such as:
antimicrobial agents, e.g. Triclosan, chlorhexidine, copper- , zinc- and stannous salts such as zinc citrate, zinc sulphate, zinc glycinate, sodium zinc citrate and stannous pyrophosphate, sanguinarine extract, metronidazole, quaternary ammonium compounds, such as cetylpyridinium chloride; bis-guanides, such as chlorhexidine digluconate, hexetidine, octenidine, alexidine; and halogenated bisphenolic compounds, such as 2,2′ methylenebis-(4-chloro-6-bromophenol);
anti-inflammatory agents such as ibuprofen, flurbiprofen, aspirin, indomethacin etc.;
anti-caries agents such as sodium- and stannous fluoride, aminefluorides, sodium monofluorophosphate, sodium trimeta phosphate and casein;
plaque buffers such as urea, calcium lactate, calcium glycerophosphate and strontium polyacrylates; vitamins such as Vitamins A, C and E;
plant extracts;
desensitising agents, e.g. potassium citrate, potassium chloride, potassium tartrate, potassium bicarbonate, potassium oxalate, potassium nitrate and strontium salts;
anti-calculus agents, e.g. alkali-metal pyrophosphates, hypophosphite-containing polymers, organic phosphonates and phosphocitrates etc.;
biomolecules, e.g. bacteriocins, antibodies, enzymes, etc.;
flavours, e.g. peppermint and spearmint oils;
other proteinaceous materials such as collagen;
preservatives; e.g. methyl paraben;
opacifying agents; e.g. titanium dioxide;
colouring agents; e.g. FD&C Blue No. 1, FD&C Yellow No. 5;
pH-adjusting agents; e.g. monosodium phosphate, trisodium phosphate, sodium hydroxide, sodium carbonate;
sweetening agents; e.g. sodium saccharin, aspartame;
pharmaceutically acceptable carriers, e.g. starch, sucrose, water or water/alcohol systems etc.;
surfactants, such as anionic, nonionic, cationic and zwitterionic or amphoteric surfactants;
particulate abrasive materials such as silicas, aluminas, calcium carbonates, dicalciumphosphates, calcium pyrophosphates, hydroxyapatites, trimetaphosphates, insoluble hexametaphosphates and so on, including agglomerated particulate abrasive materials, usually in amounts between 3 and 60% by weight of the oral care composition;
humectants such as glycerol, sorbitol, propyleneglycol, xylitol, lactitol etc.;
binders and thickeners such as sodium carboxymethyl-cellulose, xanthan gum, gum arabic etc. as well as synthetic polymers such as polyacrylates and carboxyvinyl polymers such as Carbopol®;
polymeric compounds which can enhance the delivery of active ingredients such as antimicrobial agents can also be included. Examples of such polymers are copolymers of polyvinylmethylether with maleic anhydride and other similar delivery enhancing polymers, e.g. those described in DE-A-3,942,643 (Colgate);
buffers and salts to buffer the pH and ionic strength of the oral care composition; and
other optional ingredients that may be included are e.g. bleaching agents such as peroxy compounds e.g. potassium peroxydiphosphate, effervescing systems such as sodium bicarbonate/citric acid systems, colour change systems, and so on.
Liposomes may also be used to improve delivery or stability of active ingredients.
The oral compositions may be in any form common in the art, e.g. toothpaste, gel, mousse, aerosol, gum, lozenge, powder, cream, etc. and may also be formulated into systems for use in dual-compartment type dispensers.
Particular embodiments according to the invention are illustrated with the following non-limiting examples:
EXAMPLE1
Percent by Weight
Calcium carbonate 40.00
Sorbitol 27.00
Hydrated silica 2.00
Sodium carboxymethyl cellulose 0.90
Sodium lauryl sulphate 2.00
Titanium dioxide 1.00
Sodium monofluorophosphate 0.80
Trisodium phosphate 0.50
Sodium saccharin 0.20
Flavour oil comprising 2′-hydroxypropiophenone 1.20
Water 24.40
pH = 9.7
EXAMPLE 2
Percent by Weight
Hydrated silica 18.50
Sorbitol 45.00
Polyethylene glycol 5.00
Sodium carboxymethyl cellulose 0.90
Sodium lauryl sulphate 1.50
Titanium dioxide 1.00
Sodium bicarbonate 5.00
Sodium fluoride 0.22
Sodium saccharin 0.50
Flavour oil comprising 2′-hydroxypropiophenone 1.00
Water 21.38
pH = 9.1

Claims (9)

What is claimed is:
1. Oral composition comprising a wintergreen flavour imparting ingredient and having an alkaline pH, characterised in that the wintergreen flavour imparting ingredient is 2′-hydroxypropiophenone.
2. Oral composition according to claim 1, wherein it has a pH greater than 7.5.
3. Oral composition according to claim 1, wherein it has a pH greater than 8.5.
4. Oral composition according to claim 1, wherein it comprises as a polishing agent calcium carbonate.
5. Oral composition according to claim 1, wherein it comprises sodium bicarbonate.
6. Oral composition of alkaline pH comprising 0.0001 to 1% by weight of the composition of 2′-hydroxypropiophenone as a wintergreen flavour imparting ingredient.
7. A method for imparting a wintergreen flavour to an oral composition of alkaline pH by incorporating into the composition 0.0001 to 1% by weight of the composition of 2′-hydroxypropiophenone.
8. Oral composition comprising:
(i) an effective amount of methyl salicylate to impart a wintergreen flavour to the composition;
(ii) from 0.0001 to 1% of 2′-hydroxypropiophenone by weight of the composition; and
wherein the composition has a pH ranging from about 7.5 to about 12.
9. Oral composition according to claim 8, wherein the pH is above 8.5.
US09/805,524 2000-03-14 2001-03-13 Oral composition Expired - Lifetime US6436371B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP002302065.8 2000-03-14
EP00302065 2000-03-14
EP00302065 2000-03-14

Publications (2)

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US20010031246A1 US20010031246A1 (en) 2001-10-18
US6436371B2 true US6436371B2 (en) 2002-08-20

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US (1) US6436371B2 (en)
EP (1) EP1263401B1 (en)
CN (1) CN1188106C (en)
AT (1) ATE305291T1 (en)
AU (1) AU2001242429A1 (en)
BR (1) BR0109202A (en)
DE (1) DE60113659T2 (en)
ES (1) ES2249423T3 (en)
HU (1) HU229034B1 (en)
PL (1) PL200767B1 (en)
WO (1) WO2001068044A1 (en)
ZA (1) ZA200206309B (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6893654B2 (en) 1998-09-03 2005-05-17 Jsr, Llc Two-stage transmucosal medicine delivery system for symptom relief
US20060099155A1 (en) * 2004-11-09 2006-05-11 Discus Dental Impressions, Inc. Dental whitening systems
US20070014887A1 (en) * 1998-09-03 2007-01-18 Cherukuri Subraman R Medicated chewing gum delivery system for nicotine
US8642016B2 (en) 2006-07-21 2014-02-04 Jsrnti, Llc Medicinal delivery system, and related methods

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1682079B1 (en) * 2003-11-12 2007-04-25 Symrise GmbH & Co. KG Mixture with wintergreen odor and flavor
CN103881421B (en) * 2014-03-07 2015-07-22 江苏双乐化工颜料有限公司 Nanometer surface modifier and preparation method and using method thereof
CN107444775B (en) * 2016-05-18 2020-06-12 高露洁-棕榄公司 Dentifrice package
CN112826751B (en) * 2021-01-28 2022-07-22 重庆登康口腔护理用品股份有限公司 Anti-allergy toothpaste capable of enhancing fluorine activity
GB202102675D0 (en) 2021-02-25 2021-04-14 Givaudan Sa Methods of masking off-tastes

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4844883A (en) 1987-01-20 1989-07-04 Florasynth, Inc. Stabilization of wintergreen flavor in chalk-based dentifrice and method
WO1993004664A1 (en) 1991-09-05 1993-03-18 7-L Corporation Mouthrinse and method of preparation
WO1998031242A1 (en) 1997-01-15 1998-07-23 Wm. Wrigley Jr. Company Enhanced flavors using 2'-hydroxypropiophenone
WO2000010520A1 (en) 1998-08-24 2000-03-02 Unilever N.V. Toothpaste comprising fine and coarse calcium carbonate

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4844883A (en) 1987-01-20 1989-07-04 Florasynth, Inc. Stabilization of wintergreen flavor in chalk-based dentifrice and method
WO1993004664A1 (en) 1991-09-05 1993-03-18 7-L Corporation Mouthrinse and method of preparation
WO1998031242A1 (en) 1997-01-15 1998-07-23 Wm. Wrigley Jr. Company Enhanced flavors using 2'-hydroxypropiophenone
WO2000010520A1 (en) 1998-08-24 2000-03-02 Unilever N.V. Toothpaste comprising fine and coarse calcium carbonate

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6893654B2 (en) 1998-09-03 2005-05-17 Jsr, Llc Two-stage transmucosal medicine delivery system for symptom relief
US20070014887A1 (en) * 1998-09-03 2007-01-18 Cherukuri Subraman R Medicated chewing gum delivery system for nicotine
US20060099155A1 (en) * 2004-11-09 2006-05-11 Discus Dental Impressions, Inc. Dental whitening systems
US8642016B2 (en) 2006-07-21 2014-02-04 Jsrnti, Llc Medicinal delivery system, and related methods
US10799449B2 (en) 2006-07-21 2020-10-13 Jsrnti, Llc Medicinal delivery system and related methods

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Publication number Publication date
PL357560A1 (en) 2004-07-26
US20010031246A1 (en) 2001-10-18
AU2001242429A1 (en) 2001-09-24
CN1188106C (en) 2005-02-09
PL200767B1 (en) 2009-02-27
BR0109202A (en) 2002-12-17
CN1416333A (en) 2003-05-07
DE60113659D1 (en) 2005-11-03
ATE305291T1 (en) 2005-10-15
EP1263401A1 (en) 2002-12-11
EP1263401B1 (en) 2005-09-28
DE60113659T2 (en) 2006-07-06
HUP0204539A3 (en) 2010-01-28
ZA200206309B (en) 2003-08-07
WO2001068044A1 (en) 2001-09-20
HUP0204539A2 (en) 2003-04-28
ES2249423T3 (en) 2006-04-01
HU229034B1 (en) 2013-07-29

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